


So, A Guy Walked Into A Bar

by obstinatrix



Category: Supernatural
Genre: Incest, M/M, The nature of the set-up in this story requires me to warn for potential dub-con. Also, and a bit of an open ending., obviously
Language: English
Status: Completed
Published: 2011-03-06
Updated: 2011-03-06
Packaged: 2018-10-17 06:24:45
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,757
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10588251
Author URL: https://archiveofourown.org/users/obstinatrix/pseuds/obstinatrix
Summary: In Palo Alto, CA, Dean Winchester meets a blonde with a proposition.





	

**Author's Note:**

> I wrote this for [](http://cherie-morte.livejournal.com/profile)[cherie_morte](http://cherie-morte.livejournal.com/), partly because she donated to [](http://help-nz.livejournal.com/profile)[help_nz](http://help-nz.livejournal.com/), but mostly because I am, apparently, incapable of saying no to her. ♥ Stop judging meeeee. I am aware that the pairing is made of wtf.

**Title** : So, A Guy Walked Into A Bar  
 **Rating** : NC-17  
 **Pairing** : Dean/Jess/girl!Sam  
 **Summary** : In Palo Alto, CA, Dean Winchester meets a blonde with a proposition.  
 **Words** : ~ 5,000  
 **Notes** : I wrote this for [](http://cherie-morte.livejournal.com/profile)[**cherie_morte**](http://cherie-morte.livejournal.com/) , partly because she donated to [](http://help-nz.livejournal.com/profile)[](http://help-nz.livejournal.com/)**help_nz** , but mostly because I am, apparently, incapable of saying no to her. ♥ Stop judging meeeee. I am aware that the pairing is made of wtf.  
 **Warnings** : The nature of the set-up in this story requires me to warn for potential dub-con. Also, incest, obviously, and a bit of an open ending.

Dean's picked up girls twice before in the bar he's in now, making this third attempt probably some kind of Winchester record, but, hell, it's totally not Dean's fault there are so many red-herring-hunts in Palo Alto, nor that university areas always have the best nibbles and shit. He likes this place, that's all; likes the faux-vintage prints of cars pinned up over the bar and the bosomy college girls selling shots out of holster belts - a safeguard, Dean assumes, against things getting too predictably kitsch, but hey, he'll take it. Dad wouldn't be seen dead in an upbeat little joint like this, all Broadway lights and pitchers of Corona, but Sam - Dean thinks maybe it'd be Sam's kind of thing. Not that this is in any way influencing the fact that he keeps coming back, or anything. Just a simple observation.

There's a girl on the far side of the room keeps giving him the eye, her attentions unmistakable, but somehow not what Dean would call slutty. Doesn't look drunk, either, and she's _hot_ , shit. Dean could get into that. He imagines it briefly: running his palms up the insides of those legs that seem to go all the way up to her face; her voice kinda deep, appreciative, when he touches her. She's seriously tall, probably almost as tall as Dean is, with a face that's shrewd and quick, despite the long blonde mane. Low-slung blue jeans emphasise the flare of her hips and the narrow span of her waist above them; the swell of her tits throws the _Thundercats_ print on her t-shirt into luscious distortion. Oh, man. Dean's twitching a little in his pants just at the sight of her.

Still. It's not like Dean's desperate, or anything. It's always been a point of pride to let the ladies come to _him_ , and it's a very rare occasion when _somebody_ doesn't, even if it isn't the chick he had his eye on. He turns around in his chair. "Another beer?" He holds up his empty in mock-salute.

"Coming right up," says the barman, and hell, Dean'll be damned if this kid isn't checking him out, too. Dean makes sure to smile back at him real wide, give the guy something to beat off on in his lonely dorm room, because hey, he's a giver that way.

Dean's just lifting the beer to take a sip when he spots the shape of her materialising in his peripheral vision. Damn, that was quick.

"Hey," says the chick, leaning an elbow on the bar so her whole upper body is right up in his space. She's got this voice that goes straight to his cock, does not pass go or collect two hundred dollars, and Dean has to take a moment to get his shit together, which, okay, wow.

"Hey," he shoots back, when he's sure he can actually speak without somehow making a total ass of himself. He smiles at her, and - oh, yep - there it is, the cock of her head that says she's eating it up, his face and his goddamn impeccable manners. Dean Winchester is seven kinds of irresistible gentleman.

"So," says the chick, her own smile quirking broader, "I was watching you from over there."

Direct. Dean likes it. "Kinda watchin' you back," he confesses; ducks his head a little and then smiles up at her under his eyelashes. (Edge of vulnerability: chicks dig it.)

The girl snorts. "Yeah, I got that part," she says, like she isn't exactly buying the vulnerable shit, and she reaches across the counter and picks up Dean's beer from right where it's sitting under his nose.

"Hey," Dean protests, but it's more for form's sake than anything, because, damn. This chick _is_ a Thundercat. Dean can work with that. "That's mine."

"Yeah..." says the chick, slowly, like she's talking to an idiot or something, but she grins at him around the bottleneck as she puts it to her lips; tips her head back and takes a long, deep draw. Dean watches her throat ripple all the way down as she swallows, faint sheen of sweat glinting in the hollows.

"Tell you what," the girl says; wipes her mouth and sets the beer down flat on the bar again. "How about I let you borrow something of mine, pay you back?" She smirks, and there are worlds of danger in it. Dean's cock is swiftly forgetting it's in public.

"Depends what it is," he manages, mostly smooth. "Is it gonna be worth my while?"

She gives him a conspiratorial look, and then leans closer still, the ends of her long hair brushing Dean's forearm through the leather jacket. "Well..." she begins, for the first time kind of hesitant.

Dean raises his eyebrows and takes a sip of beer.

"I was thinking my girlfriend."

Dean comes so close to spitting the beer right back out that he actually has to clamp his hand over his mouth. He takes a deep breath through his nose and swallows hastily, but the end result is a fit of coughing that makes his "Holy - " come out kind of broken and weird. The girl's laughing, though, the momentary flicker of nervousness gone, and Dean isn't sure if that's a good thing or just totally unfair, because he sure as hell is not getting any closer to his stable footing.

"Your _girlfriend_?" he gets out, eventually. "But you're - you don't - "

Her brows draw together slightly. "You were _not_ just gonna say 'you don't look like a lesbian.'"

...yeah, Dean pretty much has no answer to that except an elaborate shrug and a prayer. He tries both. To his great relief, she seems to find the haplessness kind of endearing.

"Hick," she accuses. "I'm _not_ , as it happens, but I could be. I've been with guys before, but I really can't see myself having another relationship with one."

"But...we're okay for sex," Dean says, dubiously. The girl shrugs.

"Guys are great for a lot of things," she says, unhelpfully, but Dean smirks a little. He thinks he can pretty much hear what she isn't saying.

"Sometimes a girl's just gotta get some _real_ sex, huh?"

The girl's face shuts down immediately, smile slipping off it in less than a fraction of a second. Shit. _Shit_. Wrong thing, wrong thing.

"Nobody gets to say homophobic shit like that around me, sweetheart," says the chick, low and stern and goddammit, why is Dean's dick too fucking inappropriate to know that it shouldn't be enjoying this? "It was _real sex_ when I made her scream the fucking apartment-block down last night, _believe me_. Anyone who thinks otherwise is an idiot."

Dean swallows, trying not to look as chastened as he feels as he says, "So why're you still talking to me, then?"

To Dean's enormous relief, the smile begins to edge back out again, then, as she leans closer, her mouth almost brushing his ear when she opens it to speak. "Because my girlfriend's never been with a guy before, but she wants to give it a shot. With me. For fun. So I promised her I'd bring back the hottest one I could find." She gives him a significant look and leans back. "That's you, sunshine, and I don't want to bring my girl second best. So - are you coming, or not?"

Dean's off the stool before he can stop to worry about the currently indecent state of his dick. "Okay, that would be a _hell yes_."

"Awesome," says the chick, and, yeah, standing shoulder to shoulder, they're almost the same height. "I'm Jess," she offers, slipping her hand into his.

"Dean."

She nods, squeezing a little around his fingers. "Come on, then, Dean. It's not far."

*

It's not the craziest thing he's ever done. Hell, _obviously_ most people would qualify stuff like hunting werewolves and mopping up puddles of ectoplasm from old ladies' kitchen floors as way more crazy than this, but Dean's not even counting all the hunting shit. Thinking only about sexual situations, this is not the craziest thing Dean's ever done.

As he watches Jess fumble with the keys to her apartment, though, he's pretty sure it's got to be the hottest, and so far she's only touched his hand.

It's crossed his mind that Girlfriend might actually be some kind of hideous bull-dyke, but really, Dean's into women of all varieties, even if he's partial to blondes and Asian girls, and he sort of doubts any girl would put him off just by virtue of looking more like a boy. Dean's not above doing the odd guy from time to time, and besides, it isn't really likely that anyone actively ugly could have pulled a chick like _Jess_. Dean's pretty sure she's the hottest girl he's seen in the better part of a year, and not just because of her figure. When they get inside and Jess puts the chain on the door, calls out, "Honey, I brought you something!" his heart starts to kick in his chest, racing with some mixture of curiosity and blind, spiking _want_.

Despite the brazenness Jess has displayed to this point, Dean still doesn't expect to see what he sees when they enter the bedroom. There's a girl on the bed, all long limbs and California tan, spread-eagled in her panties and a white lace balcony bra that shows off her little round tits to shocking perfection. Her dark hair is cut fairly short and her eyes and nose are entirely obscured by a blindfold, but her pale pink mouth and sharp jaw suffice to convince Dean that her face is probably just as stunning as her body, all athleticism and straight lines. He sucks in a sharp breath through his teeth at the sight of her, and Jess laughs a little beside him.

"Hot stuff, huh?"

"The hottest," Dean says, low and rough with lust and earnestness. On the bed, the girl sort of stiffens a little, and Dean guesses it's probably just the weirdness of hearing other people talking about her like this but he steps carefully forward just the same, wraps his fingers gently around her ankle. No fun pushing anyone into something they don't actually want to do.

"Hey," he says, soft and low, "You okay with this, sweetheart? No obligation just 'cause I'm here, or anything. You just say."

The girl turns her head a little, responding to the sound of his voice, and Dean's kind of afraid he's about to be bitterly disappointed. Then she digs her heels into the mattress just slightly, for purchase, and lifts her hips, tilting her pelvis upward. As if this isn't clear enough invitation, she nods a little, and Dean hears Jess groan a little behind him.

"This is Dean," Jess says. "And he's fucking beautiful, baby, you wouldn't believe. You want me to take your blindfold off, let you see?"

Dean's already grinning a little at the compliment when the girl on the bed shakes her head, sudden sharp movement, and holds out a hand. Dean has no fucking clue what that means, but apparently Jess recognises it as a pre-arranged signal, because she crawls up onto the bed, leaning down until her ear is level with the girl's mouth. The girl mutters something, then, too low for Dean to hear, and Jess nods, whispers something back. When she pulls away, Dean raises his eyebrows.

"She okay?"

Jess nods. "A little shy. She says she thinks it'll be easier if she can't see you." She laughs. "Oh - and to tell you that you _sound_ beautiful."

Dean laughs right back at that. "She can't tell me that herself?"

Jess puts a finger to her lips. "Doesn't want to talk. Like I said, she's shy."

"What's her name?"

Jess shakes her head, lips pressed together in a tight enigma of a smile, and Dean blinks at her for a moment, then shrugs. He's heard weirder. He can let 'em have their way.

"Well," he says, addressing the girl on the bed, "I'm flattered you like my voice, anyway, sweetheart. I think you're gorgeous."

The girl smiles, shifts her legs a little. She's tall, too, long thighs and square shoulders and Dean is reminded, for a moment, of Sammy the summer before she left, her long narrow back and that _smile_ and the way her breasts looked, loose in Dean's old Zeppelin shirt. Something leaps in his groin, and Dean shakes the thought firmly away. He knows he's a sick fuck, always mixing up his sex with his sister, but it doesn't usually seep in until he's a hell of a lot closer to coming. _Jesus_.

"She was in all my freshman English classes," Jess says, conversationally, and weirdly enough Dean's actually kind of interested in what she's saying, right up until she crosses her arms and pulls her t-shirt up over her head. She only grins at him, like she doesn't expect him to be able to respond, and goes on, "She's a genius, I swear." She crooks her arms up behind her back, unsnapping her bra, and she spills out of it immediately, her breasts full and heavy.

"Nguh," Dean manages, and she laughs.

"Take your clothes off for me, Dean."

Dean doesn't remember the last time he undressed so fast, unless perhaps it was that time when Sammy was fifteen and those goblin-things got 'em in Omaha, dust fucking everywhere and Dad said they had to get everything off and get in the shower before it stuck. Sam was right in the middle of her growth-spurt then, still all elbows and knees and Dean tried hard not to look for the sake of her modesty as they piled into the shower together, but he couldn't help catching flashes, the new swell of her tits and the shadowed place between her legs. Fuck.

Dean swallows down the thought (because, seriously, _really_?) and shoves jeans and underwear down in one go; hooks his thumbs in his boots and pulls the whole lot off together. He spreads his arms slightly, palms outward, like he's done some amazing trick, and Jess laughs.

"Nice," she says, and skins out of her own jeans.

Dean bites back an undignified sound in his throat. She was stunning before, but without her clothes she's a goddess, all long muscled thighs and tiny little panties that barely contain her pubic area between. As far as underwear goes, they look completely impractical, but Dean wants to get his fingers inside so bad it hurts. His neglected cock twitches against his stomach, blurts a little smear of precome. "Fuck," he whispers.

"Mmm." She steps closer, bypassing the pile of his discarded clothes, and then she's in his arms, all hot smooth skin sliding under his hands and against his chest, the softness of her breasts crushed pleasantly between them. She's almost exactly at eye-level when she leans in to kiss him, and it's odd for a second but then his eyes are closed anyway, and she's so fucking good at this that he doesn't even care. She licks at his mouth, tiny little nips at the swell of it, first, but there's nothing tentative about this; nothing uncertain about the way she parts his lips and nuzzles until they're kissing filthy and deep, slow slide of her tongue over his, ticklish drag of it up over the roof of his mouth. Dean groans into her mouth, grinds his hard dick against her thigh when she sucks on his tongue and she smiles into it, palming his hips, his ass. She's still wearing her panties, of course, but Dean figures he can work with it, fingers skimming under the waistband at the small of her back, curving around to ghost over her hipbones until she jerks against him, breath stuttering into the kiss.

"God," she breathes against his mouth, pulling away. She looks heavy-lidded, debauched, and his first instinct is to pull her back in again, but she shakes her head; indicates the bed. "Come on."

Dean doesn't need to be asked twice. Jess climbs up easily on one side of the other girl, and Dean, after a moment's hesitation, crawls up on her other side, although he's careful to maintain a little distance between them for now.

"Hey, baby," Jess says, softly, and there's something in it more than sex, something Dean doesn't often hear. The girl seems to hear it, too, turning her face towards the sound, and Jess rolls into her, breasts pressed flush against the girl's chest as she leans up on one elbow and licks at her mouth, worrying her lower lip with her teeth before she licks her way inside. It strikes Dean, as he watches, that he's never actually seen this before. He's had girls make out for him, sure, but there's something about this kiss, the gentleness and familiarity to it, that turn it into something else, something weirdly, immeasurably hotter. Dean wouldn't have chalked himself up as a sentimentalist, but, damn, apparently his dick is. He groans a little in his throat; reaches down to wrap a hand around himself, just holding lightly.

"God," he says, "that's gorgeous."

"Hmm." Jess pulls back and flashes him a smile. "You wanna see something really gorgeous?"

She doesn't wait for an answer, fingers beginning an immediate descent down over the other girl's stomach, tracing the outlines of her muscles until they find her cotton panties, incongruously respectable and innocent. The fingers don't stop, trailing down, down between the girl's legs until she draws in a breath, raising her hips into the touch, and Jess laughs a little; finds the girl's clit and circles it through her panties. The girl whimpers a little, thrusts her hips again.

"See, this," Jess says, "this is what guys always miss. Through the panties, dude. It feels so good." She draws her fingers lower, following the line of the other girl's labia through the damp cotton of her panties, and then walks them slowly back up again, pausing to tap and stroke, occasionally pressing down hard. By the time she's moved back up to the waistband of the panties, both Dean and the girl are breathless and whimpering, the girl's hips moving in restless circles, fingers clenched in the sheets.

"Okay," Jess says, and then she's hooking her fingers in the waistband of the panties, inching them down, and fuck, the girl is nothing but helpful, arching her back right up off the bed so Jess can work them over her ass and down her legs. Afterwards, she lets her thighs fall open, pelvis lifting wantonly, and God, Dean can smell her, can see the flushed nub of her clitoris, the slick wet shine of her cunt. He's shifting involuntarily even before Jess's hand finds the nape of his neck, urging him gently down.

Dean _loves_ doing this. He loves everything about it; the way the girl's muscles tense and release in her thighs, under his palms, against his neck; the way she lifts her pelvis to meet his mouth, but most of all, _fuck_ , how wet she is, the slick musky taste of her under his tongue. He searches her out, dipping into her cunt and then lapping a path back up to her clit, and she cries out, jerking against his mouth as he licks at her there, deft little circles of his tongue.

"Fingers," comes Jess's voice, rough and low, and then her mouth at the nape of his neck, sparking a shiver that coils hotly down his spine. His breath hitches, and he closes his lips around the other girl's clit, sucks until her legs jerk straight, back arching up off the bed. Jess laughs a little, mouths at him again. "C'mon, Dean, open her up. Get her ready for you."

He groans at that, can't help it, and the girl whimpers under him as the sound of it vibrates right against her clit. She's wet enough already that Dean doesn't anticipate any problem sliding on into her, but he presses two fingers in anyway, slippery-slick into the hot grasp of her cunt. She moans, muscles fluttering around him as he draws his fingers out again, then thrusts back in. It's a beautiful sound, deep and low and Dean wants more of it, suddenly; flicks his tongue over her clit again and paints circles there while he fucks in and out of her shallowly, cock hot and leaking at the way she clutches at him like she wants to keep him inside.

"Fuck," Jess gets out a little brokenly, and then she's tugging at Dean's shoulders, trying to haul him up again. Dean groans in protest, and beneath him, the girl's hips lift as if to follow him, but Jess is unrepentant.

"She's ready," she says, and then Dean sees the condom in her hand, already out of its little foil packet. His breath stops.

"Sure?" he ventures, squeezing the other girl's thigh, and it's right up there on the list of the top ten hardest things he's ever had to say. She nods, though, immediately, and when Dean glances back over at Jess, she's smiling.

"I wouldn't have pegged you for such a gentleman, you know? I'm impressed."

Dean opens his mouth. There's something stunningly intelligent right on the tip of his tongue, honestly, there _is_ , but then Jess's hand is on his cock, smoothing the condom on, and Dean can't be blamed for forgetting it. He bites his lip; rocks forward into her hand.

"Shit," he manages, articulately. "Are you - ?"

"Don't worry about me," Jess tells him, pulling herself up on her knees, facing Dean. "I want to watch." She lets go of him carefully. "Gentle, remember?"

"Oh, God." Dean wrestles off a wave of heat with a firm squeeze to the root of his cock; leans down to position himself at the wet, pink entrance of the girl's cunt. "I can be gentle," he promises, and lets himself sink.

He goes slow, careful, but her walls spread easily for him, hips snapping up as he bottoms out inside her, her head falling back on a silent cry. She's hot around him, tight and slick and incredible, but he pauses inside her, all the same, giving her a moment to accommodate the stretch of him, the burn of his cock splaying her open. He wants to thrust, every impulse in his body arrowing down to that thudding heat between his legs, but fuck, he wants to make her come first. This is a first for her, he thinks; maybe it'll be the only time. These girls love each other, an idiot could see that. If this is going to be the only time she has a man inside her, he wants to make sure she remembers it, remembers _him_ ; there's something feral in Dean that wants to brand this girl with his mark from the inside out, love her so deep she'll never be able to leave him behind.

He doesn't even know her name. Beside them, Jess has worked one hand into her panties, fingers slipping wetly in and out of herself, and her laboured breathing makes Dean clench up with want, adds another layer to the intensity of it, of them. "Do it," Jess gets out, hitched as her pelvis hitches upward, too, and God, what can it fucking hurt? Dean doesn't even know her name.

"Sam," he breathes, the word a long, low whine as the urgency building in his hips takes over, fucking him forward into the soft heat of her body. Somewhere to his left, he hears Jess's breath catch on a gasp, but he's lost somewhere beyond that, now, lost in this girl underneath him with her legs and her mouth and a jawline he can't look away from. He wraps a hand around her waist, coaxing her into a rhythm and she goes with it, hips slamming up into his, jamming him deep and hard inside of her.

"Sammy," he hears himself say, though he'd give anything not to, "fuck, Sammy, Sammy, Jesus," and she's grasping at his shoulders, pulling him down, long-fingered hands roving over his shoulders and up into his hair. He goes with it, licking blindly at her breathless mouth until she opens for him, sucking on his tongue and rolling her pelvis up against him in desperate, unpractised little motions. She's perfect, he thinks, so hot and tight and clinging to him, legs around his waist, hands stroking everywhere, brushing his nipples and the sensitive dip of his spine. He moans, and she clenches around him, fucks up harder, like she doesn't mind hearing another girl's name while she loses her boy-virginity; fucks up onto him like she's hearing her own.

"Oh, Jesus," he murmurs against her slack mouth, hips jackhammering into her, derailed and desperate with the thought of it.

"Dean," Sam says in his mind, choked-off gasping moan and then she's coming, clenching around him in helpless flutters and she cries out, "Dean!" and fuck, Jesus _fuck_. It's her.

Dean digs his fingers into her shoulders and comes like he's dying.

For a long, long moment afterwards, it's as if Dean's mind has shut itself off to everything but white noise. When, at last, he succeeds in raising his head, the first thing he sees is Jess, lax and spread-eagled on the bed with her thighs loose and open, fingers playing lazily in the mess of slick between them. The smile she throws him is quizzical, although her expression is mostly warm, sated drowsiness, the quiet after climax. Dean swallows.

"Sam," he says. It comes out hoarse, like his throat doesn't want to work.

"Yeah." It's her voice; he'd know it anywhere. He doesn't know if he dares look at her. He's still _inside_ her, for fuck's sake; and yet he isn't pulling out. Why the fuck isn't he pulling out?

Then Sam's hands settle in his hair, soft and tentative and gentle and he remembers how careful she was, the whole time, not to speak; her insistence on retaining the blindfold. How far back did this go? How - "When did you know it was me?"

Sam laughs nervously, fingers pushing strands of Dean's hair behind his ear, over and over again. "When you spoke," she said, faintly. "Dean, I - I'm sorry."

Dean takes a deep breath, then, and looks up. She's taken the blindfold off, as he suspected, and God, there's his Sammy, hazel eyes and the familiar slope of her nose. She's clutching one of Jess's hands, he notices, dimly. Like she's waiting for something. Like she's afraid of him.

"Don't be sorry," Dean says. "It's not - " He cuts himself off with a snort. "Well, no, okay, it is your fault. But you're not the one that's fucked up, Sammy."

Sam laughs, short and brittle but there's relief in it, something tentatively like hope. "Dean, come on. I think we're pretty much both fucked up beyond all redemption, here." Her fingers stroke over his cheekbone, the upper curve of his ear. "Call it even?"

She smiles at him, that same stupid smile he's never been able to resist, and he's already smiling reluctantly back at her when Jess jerks suddenly, as if something's just fallen into place.

"Oh, God," she says, abruptly. "Sam, you're not telling me that's - _him_?"

Dean's stomach, which had just begun to uncoil, goes immediately cold again. "Look," he begins, without any knowledge of how he means to go on, "I just..."

But Jess is shaking her head, kneading Sam's hand tight and close between her fingers. "It's okay," she says, soft and low, like someone comforting an animal. "It's okay, babe." Her mouth quirks a little, hesitant, but there. "I guess if _he_ were my brother, I might be holding out for him, too."

It's not funny, really, but that doesn't stop Dean laughing. If nothing else, this Jess chick is...yeah. Sammy could have done one hell of a lot worse.


End file.
